WO2010135194A1 - Composés biocides à base d'amide halogéné et procédés de traitement de systèmes aqueux à un ph proche du neutre à élevé - Google Patents

Composés biocides à base d'amide halogéné et procédés de traitement de systèmes aqueux à un ph proche du neutre à élevé Download PDF

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Publication number
WO2010135194A1
WO2010135194A1 PCT/US2010/034936 US2010034936W WO2010135194A1 WO 2010135194 A1 WO2010135194 A1 WO 2010135194A1 US 2010034936 W US2010034936 W US 2010034936W WO 2010135194 A1 WO2010135194 A1 WO 2010135194A1
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WIPO (PCT)
Prior art keywords
water
oil
membrane
formula
gas
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Application number
PCT/US2010/034936
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English (en)
Inventor
Bei Yin
Steven Rosenburg
Steven D. Jons
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Dow Global Technologies Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Dow Global Technologies Inc. filed Critical Dow Global Technologies Inc.
Priority to BRPI1007575-5A priority Critical patent/BRPI1007575B1/pt
Priority to MX2011012350A priority patent/MX2011012350A/es
Priority to JP2012511913A priority patent/JP5635596B2/ja
Priority to EP10719521.6A priority patent/EP2432738B1/fr
Priority to RU2011151714/04A priority patent/RU2542979C2/ru
Priority to CN201080021782.7A priority patent/CN102428035B/zh
Publication of WO2010135194A1 publication Critical patent/WO2010135194A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/72—Treatment of water, waste water, or sewage by oxidation
    • C02F1/76—Treatment of water, waste water, or sewage by oxidation with halogens or compounds of halogens
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/30—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the groups —CO—N< and, both being directly attached by their carbon atoms to the same carbon skeleton, e.g. H2N—NH—CO—C6H4—COOCH3; Thio-analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/42—Treatment of water, waste water, or sewage by ion-exchange
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
    • C02F1/441—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis by reverse osmosis
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
    • C02F1/442—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis by nanofiltration
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/44—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis
    • C02F1/444—Treatment of water, waste water, or sewage by dialysis, osmosis or reverse osmosis by ultrafiltration or microfiltration
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/70—Treatment of water, waste water, or sewage by reduction
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/10—Inorganic compounds
    • C02F2101/101—Sulfur compounds
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2303/00—Specific treatment goals
    • C02F2303/20—Prevention of biofouling

Definitions

  • the invention relates to methods for controlling microorganisms in water systems that contain one or more reducing agents.
  • Water systems provide fertile breeding grounds for algae, bacteria, viruses, fungi, and other pathogens. Microbial contamination can create a variety of problems, including aesthetic unpleasantries such as slimy green water, serious health risks such as fungal, bacterial, or viral infections, and clogging or corrosion of equipment.
  • Biofouling of water systems susceptible to microbial contamination is typically controlled through the use of biocidal agents.
  • biocidal agents 2,2-dibromo-3- nitrilopropionamide
  • DBNPA 2,2-dibromo-3- nitrilopropionamide
  • DBNPA 2,2-dibromo-3- nitrilopropionamide
  • Sulfites, bisulfites, and sulfides are reducing agents that are known to quickly deactivate biocides such as 2,2- dibromo-3-nitrilopropionamide (DBNPA), rendering the biocides prematurely ineffective. It would be a significant advance in the art to provide biocides that are fast acting, long lasting, and that are stable when subjected to potentially deactivating conditions in the water system, such as the presence of reducing agents.
  • DBNPA 2,2- dibromo-3-nitrilopropionamide
  • the invention provides a method for controlling microorganisms in a water system that contains a reducing agent.
  • the method comprises treating the water system with an effective amount of a compound of formula I:
  • the invention relates to methods for controlling microorganisms in water systems that contain one or more reducing agents.
  • the method comprises treating such a water system with a compound of formula (I).
  • the inventors have surprisingly discovered that compounds of formula (I) are more resistant to deactivation by reducing agents in the water system than other biocides, including the commercial compound
  • DBNPA 2,2- dibromomalonamide
  • DBNPA a comparative biocide
  • X in the compounds of formula I is bromo, chloro, or iodo, more preferably it is bromo.
  • a preferred compound of formula (I) is 2,2-dibromo-2-cyano-N-(3- hydroxypropyl)acetamide.
  • a further preferred compound of formula (I) is 2,2-dibromomalonamide.
  • 2,2-dibromomalonamide means a compound of the following formula:
  • the compounds of formula I are useful for controlling microorganisms in water systems that contain reducing agent.
  • water systems include, but are not limited to, paper and pulp mill stock tank and process water, paper making white water, oil and gas field injection, fracturing, and produced water, oil and gas wells and reservoirs, deaeration tower, oil and gas operation and transportation systems, oil and gas field functional fluids, oil and gas wells and reservoirs, oil and gas separation system and storage tanks, oil and gas pipelines, gas vessels, ballast water, metal working fluids, leather making systems and membrane-based filtration systems.
  • Preferred water systems are paper and pulp mill process water, paper making white water, oil and gas field injection or fracturing or produced water or fluids, metal working fluids and membrane-based filtration systems.
  • reducing agent in the water systems of the invention can result from a variety of sources.
  • the process water white water
  • the process water can contain carryover sulfite, a reducing agent, from treatment of the paper stock with sodium sulfite.
  • bisulfite is added to injection or fracturing water or fluids as oxygen scavenger.
  • certain microorganisms that reside within industrial water can produce reducing metabolites such as hydrogen sulfide, also a reducing agent.
  • reducing agents that may be found in the water systems include, but are not limited to, sulfite ion, bisulfite ion, or sulfides such as hydrogen sulfide.
  • the water system of the invention contains between about 5 and about 200 ppm, more preferably between about 10 and about 100 ppm by weight of reducing agent.
  • the compounds of the invention are also surprisingly more resistant to hydrolysis at near-neutral-to-alkaline pH than other biocides.
  • DBMAL 2,2- dibromomalonamide
  • the compounds of formula (I) are used in a method for controlling microorganisms in a water system that contains a reducing agent, wherein the water system has a pH of 5 or greater. .
  • the pH is 6 or greater.
  • the pH is 7 or greater.
  • the pH is 8 or greater.
  • Representative membrane-based filtration systems include those comprising one or more semi -permeable membranes, including but not limited to: microfiltration, ultrafiltration, nanofiltration, reverse osmosis and ion-exchange membranes.
  • Applicable systems include those comprising a single type of membrane (e.g. microfiltration) and those comprising multiple types of membranes (e.g. ultrafiltration and reverse osmosis).
  • a membrane-based filtration system may comprise an upstream microfiltration or ultrafiltration membrane and a downstream nanofiltration or reverse osmosis membrane.
  • the subject biocidal compounds may be added to a feed solution prior to filtration, (e.g. added to a storage tank or pond containing feed solution to be treated) or during filtration, (e.g. dosed into a pressurized feed solution during filtration).
  • the subject biocidal compounds may be added to cleaning or storage solutions which contact the membrane.
  • any aqueous solution e.g. raw feed water, cleaning solution, membrane storage solution, etc.
  • the feed solution comprises a storage solution in which a membrane is immersed.
  • US 7,156,997 describes an exemplary package assembly for storing membranes.
  • the subject biocidal compounds When used within a system having both micro or ultrafiltration and nanofiltration or reverse osmosis membranes, the subject biocidal compounds provide biocidal effect to each membrane (e.g. both upstream and downstream membranes).
  • the portion of biocidal compound rejected by a membrane(s) may be recovered from the concentrate stream and recycled for use in subsequent treatments, (e.g. directed back to a storage tank or dosed within incoming feed).
  • the recycle of biocidal compounds may be part of an intermittent or continuous process.
  • the pH of the feed solution is at least 7, often at least 8, in some embodiments at least 9, and in other embodiments at least 10. Examples of such membrane-based systems are described US 6,537,456 and US 7,442,309.
  • membranes of many systems are commonly cleaned or stored with feed solutions having pH values of at least 11 and in some embodiments at least 12.
  • the subject biocidal compounds remain effective under such neutral and alkaline conditions.
  • the subject biocidal compounds may be added to a wider breath of feed solutions (e.g. pH adjusted aqueous feeds, aqueous cleaning solutions, aqueous storage solutions) used in connection with membrane-based filtration systems.
  • feed solutions e.g. pH adjusted aqueous feeds, aqueous cleaning solutions, aqueous storage solutions
  • the type of membranes used in such systems are not particularly limited and include flat sheet, tubular and hollow fiber.
  • One preferred class of membranes include thin-film composite polyamide membranes commonly used in nanofiltration and reverse osmosis applications, as generally described in US 4,277,344; US 2007/0251883; and US 2008/0185332. Such nanofiltration and/or reverse osmosis membranes are commonly provided as flat sheets within a spiral wound configuration.
  • Polyamide membranes are sensitive to many of chlorine compounds (e.g. chlorine, hypochlorous acid, hypochlorite) which are commonly used to disinfect water systems.
  • reducing agents such as bisulfite, sulfite or sulfide are often added to feed solutions at a point upstream from the polyamide membrane.
  • the subject biocidal compounds are more resistant to deactivation by such reducing agents.
  • microfiltration and ultrafiltration membranes include porous membranes made from a variety of materials including polysulfones, polyethersulfones, polyamides, polypropylene and polyvinylidene fluoride. Such micro and ultrafiltration membranes are commonly provided as hollow fibers.
  • the compounds of formula I can be used in the water system with other additives such as, but not limited to, surfactants, ionic/nonionic polymers and scale and corrosion inhibitors, oxygen scavengers, and/or additional biocides.
  • additives such as, but not limited to, surfactants, ionic/nonionic polymers and scale and corrosion inhibitors, oxygen scavengers, and/or additional biocides.
  • the compounds described herein are surprisingly resistant to deactivation by reducing agents than other biocides, including the commercial compound DBNPA.
  • the compounds consequently are useful for controlling microorganisms in a broader range of water systems than currently known biocides and therefore represent a significant advance to the industry.
  • microorganism means bacteria, algae, and viruses.
  • control and controlling should be broadly construed to include within their meaning, and without being limited thereto, inhibiting the growth or propagation of microorganisms, killing microorganisms, disinfection, and/or preservation.
  • hydroxyalkyl is meant an alkyl group (i.e., a straight and branched chain aliphatic group) that contains 1 to 6 carbon atoms and is substituted with a hydroxyl group. Examples include, but are not limited to, hydroxymethyl, hydroxyethyl, 2-hydroxypropyl, 3- hydroxypropyl, and the like. 5 "Halogen” refers to fluoro, chloro, bromo, or iodo.
  • ratios, percentages, parts, and the like used herein are by weight.
  • DBNPA 2,2-Dibromo-3-nitrilopropionamide
  • DBMAL 2,2-Dibromomalonamide
  • Glutaraldehyde is obtained from The Dow Chemical Company.
  • Alkyl dimethyl benzyl ammonium chloride (ADBAC) is obtained from Lonza.
  • l-Bromo-3-chloro-5,5-dimethylhydantoin (“BCDMH”) is obtained from Clariant 20 Corporation.
  • Dilute solutions (less than 0.5 wt%) of DBMAL and DBNPA are prepared at three different pHs. The pH is set and maintained, by using standard buffer solutions, at pH 6.9, 8.0 and 9.0. These solutions are then held at constant temperature at either -1 0 C or 30 0 C. Periodically, aliquots are analyzed by HPLC to determine the level of DBMAL or DBNPA 15 remaining. Results are shown in Table 1. Table 1.
  • DBMAL and DBNPA are pre-mixed with sulfite by adding to a paper mill white water sample (at about pH 7.5) containing 80 ppm sulfite. 50 ppm to 80 ppm sulfite is representative of a sulfite level for pulp and paper applications. The same white water sample without sulfite is used as none sulfite comparison and the same Whitewater samples
  • DBMAL and DBNPA are added to a contaminated paper mill white water sample (approximately 10 6 CFUAnL bacteria, pH 7.6) containing about 80 ppm sulfite, at final active biocides concentrations of 50 ppm and 25 ppm.
  • contaminated paper mill white water sample approximately 10 6 CFUAnL bacteria, pH 7.6
  • the same contaminated Whitewater samples without biocide are used as controls.
  • the mixtures are incubated at 37 0 C with shaking (100 RPM) for 96 hrs.
  • the valid bacteria in the mixtures are enumerated using a serial dilution method and the bacterial log 10 reduction is calculated by comparing the valid bacteria number of biocide treated water aliquots to that of controls.
  • the mixtures are reinoculated with field isolated bacteria at about 10 5 CFU/mL and are supplied with additional sulfite to keep an 80 ppm sulfite concentration.
  • Table 3 shows the efficacy of DBMAL and DBNPA at different time point, expressed as log 10 reduction in numbers of bacteria.
  • DBMAL shows an initial slower killing action than DBNPA, however, its effectiveness (>3 log 10 killing) lasts for two more days than that of DBNPA at the same active concentration of 50 ppm and lasts for one more day than that of DBNPA at the same active concentration of 25 ppm.
  • Biocidal Efficacy in Presence of Sulfite Comparison of DBMAL and Other Biocides Sterile artificial White Water (111 mg of CaCl 2 , 60 mg of MgSO 4 , 168 mg of
  • NaHCO 3 140 mg of K 2 HPO 4 , 480 mg of NH 4 Cl, 1.04 mg of FeCl 3 .6H 2 O, 1.48 mg of Na 2 EDTA, 3000 mg of Dextrose, 10 mg of Yeast Extract, in IL water, pH 8.1) is contaminated with field isolated bacteria at a concentration of approximately 10 7 CFU/mL. The aliquots of this contaminated water are then treated with eight dosage levels of DBMAL and six other commonly used biocides in paper mill white water application. The same aliquots of the contaminated water without biocide are used as controls.
  • the valid bacteria in the aliquots are enumerated using a serial dilution method and the bacterial log 10 reduction is calculated by comparing the valid bacteria number of biocide treated water aliquots to that of controls.
  • Table 4 compares the efficacy of the seven biocides, expressed by bacterial log 10 reduction. As indicated, DBMAL is one of most effective molecules in this comparison study.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • Water Supply & Treatment (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Hydrology & Water Resources (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Treatment Of Water By Oxidation Or Reduction (AREA)

Abstract

La présente invention a pour objet des procédés permettant de réguler les micro-organismes dans des systèmes aqueux qui contiennent un ou des agents réducteurs. Les procédés comprennent le traitement du système aqueux avec une quantité efficace d'un composé de la formule I, X, R et R1 étant tels que définis ici. La présente invention a également pour objet un procédé permettant de réguler les micro-organismes dans un système aqueux, le procédé comprenant le traitement du système aqueux avec une quantité efficace d'un composé de formule (I) : (Formule I), X étant un halogène ; et R et R1 étant, respectivement, un hydroxyalkyle et un radical cyano (-C=N), ou R et R1 étant, respectivement, l'hydrogène et un radical amido de la formule : (Formule II), le système aqueux contenant un agent réducteur tel qu'un sulfite, un bisulfite ou un sulfure.
PCT/US2010/034936 2009-05-18 2010-05-14 Composés biocides à base d'amide halogéné et procédés de traitement de systèmes aqueux à un ph proche du neutre à élevé WO2010135194A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BRPI1007575-5A BRPI1007575B1 (pt) 2009-05-18 2010-05-14 Método para controlar micro-organismos em um sistema aquoso
MX2011012350A MX2011012350A (es) 2009-05-18 2010-05-14 Compuestos biocidas de amida halogenada y metodos para tratar sistemas de agua a ph casi neutro a alto.
JP2012511913A JP5635596B2 (ja) 2009-05-18 2010-05-14 ハロゲン化アミド殺生物化合物および中性近傍から高ｐＨで水系を処理する方法
EP10719521.6A EP2432738B1 (fr) 2009-05-18 2010-05-14 Traitement de l'eau avec du 2,2-dibromo-malonamide dans un système contenant un agent réducteur ainsi que l'utilisation de 2,2-dibromo-malonamide
RU2011151714/04A RU2542979C2 (ru) 2009-05-18 2010-05-14 ГАЛОГЕНИРОВАННЫЕ АМИДНЫЕ БИОЦИДНЫЕ СОЕДИНЕНИЯ И СПОСОБЫ ОБРАБОТКИ ВОДНЫХ СИСТЕМ ПРИ pН ОТ ПОЧТИ НЕЙТРАЛЬНОГО ДО ВЫСОКОГО
CN201080021782.7A CN102428035B (zh) 2009-05-18 2010-05-14 卤化酰胺杀生物化合物和处理处于接近中性至高pH的水体系的方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17915909P 2009-05-18 2009-05-18
US61/179,159 2009-05-18

Publications (1)

Publication Number Publication Date
WO2010135194A1 true WO2010135194A1 (fr) 2010-11-25

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PCT/US2010/034936 WO2010135194A1 (fr) 2009-05-18 2010-05-14 Composés biocides à base d'amide halogéné et procédés de traitement de systèmes aqueux à un ph proche du neutre à élevé

Country Status (8)

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US (1) US20100314316A1 (fr)
EP (1) EP2432738B1 (fr)
JP (1) JP5635596B2 (fr)
CN (1) CN102428035B (fr)
BR (1) BRPI1007575B1 (fr)
MX (1) MX2011012350A (fr)
RU (1) RU2542979C2 (fr)
WO (1) WO2010135194A1 (fr)

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CN103442562B (zh) * 2011-03-25 2016-01-06 陶氏环球技术有限公司 二溴丙二酰胺的组合物及其作为杀生物剂的用途
US8754083B2 (en) * 2012-02-01 2014-06-17 Dow Global Technologies Llc Compositions of dibromomalonamide and their use as biocides
US11608516B2 (en) * 2015-04-15 2023-03-21 Ecolab Usa Inc. Method for determination of diversity and viability thresholds used to assess microorganisms in process samples
FI130853B1 (fi) * 2016-05-13 2024-04-25 Kemira Oyj Koostumus ja menetelmä mikrobien ja/tai bakteeristen itiöiden kvantitatiiviseen vähentämiseen massasuspensiossa
CN110402394B (zh) * 2017-03-01 2024-04-26 豪夫迈·罗氏有限公司 用于将关于分析物的存在的生物样品进行分类的系统和方法
JP7258944B2 (ja) * 2021-05-13 2023-04-17 水ｉｎｇ株式会社 下水のウイルス消毒剤、下水中のウイルス消毒方法及びウイルス消毒剤を用いた下水処理装置

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EP2432738B1 (fr) 2017-03-01
CN102428035A (zh) 2012-04-25
RU2542979C2 (ru) 2015-02-27
BRPI1007575A2 (pt) 2017-09-19
BRPI1007575B1 (pt) 2019-10-15
CN102428035B (zh) 2014-07-23
EP2432738A1 (fr) 2012-03-28
JP2012527351A (ja) 2012-11-08
RU2011151714A (ru) 2013-06-27
JP5635596B2 (ja) 2014-12-03
US20100314316A1 (en) 2010-12-16

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